Obsessed: The Podcast

‘Colbert Report’ Co-Creator Misses the Old Stephen

49 min
Apr 11, 20268 days ago
Listen to Episode
Summary

Ben Carlin, co-creator of The Colbert Report and head writer of The Daily Show, discusses his career trajectory from late-night satire to narrative storytelling, including his work on the new Amazon series Bait starring Riz Ahmed. He reflects on the evolution of political comedy, the challenges of sustaining daily late-night shows, and why he left the genre before the Trump era.

Insights
  • Daily late-night shows create unsustainable burnout due to nightly scripted content demands, making weekly formats like John Oliver's model more viable for long-term creative sustainability
  • The most successful comedy projects require genuine creative alignment between collaborators—a 'Venn diagram overlap' where sensibilities intersect while each party brings distinct value
  • Political satire's effectiveness depends on maintaining character authenticity and humanity; audiences connect when performers are vulnerable and flawed rather than purely cynical
  • Late-night television as a format is declining due to changing media consumption patterns, making it increasingly difficult to justify shows economically regardless of political considerations
  • Narrative comedy allows for tonal experimentation and genre-shifting that daily news-based shows cannot sustain, offering creative freedom that attracts established late-night talent
Trends
Migration of late-night talent toward limited-series and streaming formats with reduced production frequencyIncreased emphasis on character-driven comedy over topical news commentary in prestige televisionStreaming platforms (Amazon, HBO Max, Hulu) becoming primary venues for experimental comedy and narrative projectsDecline of traditional late-night television as economically viable format despite cultural relevanceRise of podcast and alternative media formats as outlets for political commentary previously dominated by cable news satireCollaborative development models emphasizing creative alignment over hierarchical production structuresTonal experimentation and genre-blending becoming expected in prestige comedy seriesIP licensing becoming more flexible for creative projects when platforms own underlying rights
Companies
Amazon Prime Video
Platform distributing Bait; acquired James Bond IP rights, affecting show development and marketing strategy
Comedy Central
Original network for The Daily Show and The Colbert Report; provided platform for Carlin's early career success
The Onion
Carlin was editor before moving to Los Angeles; influenced The Daily Show's comedic approach and sensibility
HBO Max
Distributed Carlin's series Minx; represents streaming alternative to traditional cable comedy
Hulu
Distributed Carlin's series Future Man; part of his post-late-night narrative storytelling portfolio
Fox
Developed competing late-night shows with Carlin before The Daily Show opportunity emerged
Pixar
Carlin worked on movie project during his transition from late-night to narrative storytelling
ABC
Network for Modern Family, where Carlin worked as writer during late-night career transition
HBO
Network for John Oliver's Last Week Tonight; model show Carlin and Stewart discussed developing
CBS
Network that cancelled The Late Show with Stephen Colbert; subject of discussion about late-night economics
People
Ben Carlin
Co-creator of The Colbert Report and head writer of The Daily Show; guest discussing career evolution
Stephen Colbert
Subject of discussion; Carlin co-created The Colbert Report with him and reflects on his late-night transition
John Stewart
Carlin was head writer under Stewart; discussed as model for sustainable late-night format evolution
Riz Ahmed
Star and creator of Bait; collaborated with Carlin on show development and creative direction
Matt Wilstein
Host of Obsessed podcast conducting interview with Carlin
Steve Carell
Correspondent on The Daily Show; discussed as talent Carlin and Stewart worked to retain
Patrick Stewart
Provided voice performance as Riz Ahmed's character's inner voice in Bait; discussed as casting coup
Barbara Broccoli
James Bond IP rights holder; approved Bait's use of Bond references before Amazon acquisition
Samantha Bee
Correspondent on The Daily Show during Carlin's tenure; part of 'murderers row' of talent
Ed Helms
Correspondent on The Daily Show; discussed as part of talent pool Carlin and Stewart managed
Rob Cordray
Correspondent on The Daily Show; part of ensemble talent discussed by Carlin
Conan O'Brien
Discussed as model for successful late-night talent transition to podcasts and specials
John Oliver
Model for weekly late-night format; discussed as alternative Carlin and Stewart considered
Craig Kilborn
Original host of The Daily Show before John Stewart; context for show's format evolution
Tina Fey
Carlin discussed wanting to work on 30 Rock but logistics prevented collaboration
Val Kilmer
Discussed as hero figure who visited Daily Show offices during career transition period
Quotes
"I have a soft spot for the Colbert Report, not just because I was there at the beginning, but just because it felt like it was really, really trying to do something different in that late night space."
Ben CarlinOpening and closing remarks
"When you're in that late night world for a while, you have a choice: stay when the water is really warm and nice, or try doing something else. I'd always really been interested in narrative storytelling."
Ben CarlinEarly in interview
"The reward for doing an amazing show is you get to get up and do the exact same thing tomorrow and like be disappointed if it's not as good as the show you just did."
Ben CarlinDiscussion of late-night burnout
"I think it would have been very difficult for me to kind of handle that transition when Trump came on the scene because I find it so revolting that it's just hard for me to be like, I'm going to make a joke."
Ben CarlinReflection on leaving before Trump era
"You need that Venn diagram where you overlap in some key areas, but also both are bringing something different and special to make a sum that's greater than its parts."
Ben CarlinDiscussion of creative collaboration
Full Transcript
I have a soft spot for the Colbert Report, not just because I was there at the beginning, but just because it felt like it was really, really trying to do something different in that late night space. And when you go to these big institutional shows, ultimately, you're kind of a slave to that format. And you can make it your own. I think Stephen has done a great job doing that. But I just am so much more partial to a whole idea of Colbert Nation. There was just so much about it that kind of ahead of its time. Hello and welcome to Obsessed, the podcast. I'm Matt Wilstein from The Daily Beast. And today on the show, I am talking to a writer and producer who not only helped launch the daily show with John Stewart, but also co-created the Colbert Report with Stephen Colbert. His new show is a very different kind of comedy series called Bait, starring the British actor Riz Ahmed as a fictionalized version of himself who gets the chance to audition to be the next James Bond. Ben Carlin, welcome to Obsessed, the podcast. Thank you. It's a pleasure to be here. Thank you so much for being here. So I have to tell you, I'm kind of a late night TV obsessive. I grew up watching The Daily Show and the Colbert Report and love those shows. So I knew your name from sort of behind the scenes of that show. So I was sort of surprised to see it in the credits for this new show, Bait, which I also love. But I'm curious if it felt like a departure for you, something different. Not really for me, just because you have a choice when you're in that late night world for a while, which is like stay when the water is really warm and nice, or tries doing something else. And I'd always really been interested in narrative storytelling. So after eight, nine years in late night, I wanted to take a chance and do more narrative work. So I'd since I left those shows, I've been writing sitcoms and I've done a few movies and worked on a whole bunch of streaming shows. So, you know, in the larger context of what I've been doing for the last, you know, 15, 20 years, I think the show makes a lot of sense. You know, I've always been attracted to kind of smart, funny, interesting, a little offbeat, you know, material of how it doesn't matter what, you know, what medium, as long as it kind of meets those criteria, I'm happy to do it. Yeah, well, we should say I think it's been, what, 20 years since you left late night TV. So you had time to do some other stuff. There have been, yes, there has been some, there's been some downtime, but there's been some fertile time as well. I worked on Modern Family. I've worked on a movie for Pixar. I did, you know, this show for Hulu, which I loved called Future Man. I did another show called Minks. That was on HBO Max. So I've kind of been dabbling in narrative storytelling for the last 15, 20 years or so. Well, I do want to talk about that late night stuff later on, but let's start with Bate, because as I said, I just, I love this show. I, from the log line, I was in, but then I really was taken by the whole tone of it and the, and the way that you guys put it together. It's this great, you know, six episodes on Prime Video, which is, you know, they sort of fly by and I couldn't stop watching. Can you tell me the story behind linking up with, with Riz Ahmed, who created the show and, and stars in it? Yeah, for sure. I mean, I was always a huge fan of Riz from afar. I'd never met him or worked with him, although I did have a few friends who had worked with him. So when I just kind of heard, you know, kind of talk that there was a show in the works and that they were and they had done some work on it. They had this thing called the mini room, which is kind of a thing that they, they're not doing as much anymore, but they kind of started it and tried to figure some stuff out and they'd gotten, you know, a little bit down a road, but weren't 100% happy with where it was going. And they're like, let's just kind of bring someone else in. My name got thrown into the mix just through, you know, professional circles and, you know, hopefully, you know, do enough work, you have enough of a reputation, at least get you the meeting. And so Riz and I met and we hit it off with real meeting up the minds and it was very similar. You know, I have, you know, all the good projects that I've been a part of, you know, going all the way back to working with John Stewart, you know, you have that first meeting and you just know whether this is someone you vibe with, whether this is somewhat the sensibility that you can work with, you know, shared, you know, sense of humor, you know, point of view, whatever that is, you know, you need that bend diagram where you overlap in some key areas, but also both are bringing something different and special to, you know, make a sum that's greater than its parts. So I kind of felt this had that, you know, those ingredients. But when I first met with Riz, you know, there were a ton of ideas, like a massive amount of ideas, but there wasn't really a shape to the show, a shape to the narrative, a kind of thrust. And, you know, the thing that I did, you know, I'm kind of most proud of is really drill down with him, even before we had hired writers and just figure out, you know, this kind of bond narrative and figure out, like, how could we make this like a kind of a cracker jack story. And then we both really, really liked the idea of being wildly variant in tone and just, you know, having a show that, you know, especially looking back at shows that we really like like Atlanta and Master of None, that really take some big swings with from episode to episode, you know, with narrative, you know, styles and points of view and even just genre. So I love that. And Riz was also very interested in that. So we really connected on, let's just make six, like, kind of wild episodes that tell a coherent story, but really don't let you get your footing, you know, for any, you know, long period of time. And that was something that was really exciting to me creatively and felt like new, new territory that I dabbled into a little bit in some other stuff. But this was a real feast for that. Yeah, the shifts in tone and sort of what you're able to accomplish there, I think is incredible because you have Riz Ahmed, who is a Oscar nominated dramatic performer, who is giving this very intense dramatic performance at times within the context of this often pretty absurd, very funny show. So what was it like working with him to find those moments and figure out what that what that tone should be? Because it is it gets like very emotional at times, but without losing the narrative thrust of the comedy. Yeah, I mean, his I mean, he's in person a very funny guy. But you know, if you look at his kind of choices, certainly they gravitate towards more intense dramatic, although he had done some comedy early on, he had done this amazing movie called Four Lions back, you know, early on in his career. So, you know, I think that when you're doing comedy, for me, you know, you have to just kind of start with character, you know, the situation will kind of come from, you know, understanding who this character is and what their drive is. So we really wanted to make sure that the character kind of was like a warts and all kind of character. And he was really, really game for presenting a version of himself that if people thought this was who he really was, it's oftentimes not the most flattering portrait. But there's enough humanity and enough, you know, kind of earnestness that you root for him in spite of the fact that maybe he's making some choices that you think are, you know, horrible. So that's comedic right there is to have a character who's not afraid to be ugly and vulnerable and play it be a fool. So I felt very good about grounding the show in that kind of character and that performance. And then story wise, it was a lot of trial and error. I mean, this was probably a greater volume of work done to finish product on this show than almost anything I'd ever done. There was a lot of stuff that we tried. So what you're seeing is, you know, ideally, like, you know, the best of the best, like the creed, you know, but there's a lot of there's a lot of stuff we tossed that was too broad or too serious or too confusing. And, you know, part of the reason why these episodes fly is because I'm a, you know, merciless editor and we I really wanted, you know, if it wasn't working and it was anyway not additive, I was like, let's just cut it and just make this thing sing. And he was, you know, again, he was totally agreeable to that as well. Spring is in full swing. And I know you probably have plans for Night of Fun with Friends. So here's a product to help you wake up well after a night at the bars. It's called Z Biotics Pre-Alcohol Probiotic Drink. And it's a genetically engineered probiotic invented by PhD scientists. And here's how it works. When you drink, alcohol gets converted into a toxic byproduct in the gut. It's a buildup of this byproduct, not dehydration, that's a blame for rough days after drinking. Z Biotics Pre-Alcohol Probiotic Drink enables your body to produce an enzyme that helps break down this toxic byproduct from alcohol. Just take pre-alcohol before you hit the town, drink responsibly, and you'll feel like yourself the next day. Just go to Zbiotics.com forward slash dailybeasts and use code dailybeasts at checkout for 15% off your first order. And if you're not satisfied, they offer a 100% money back guarantee. The other really interesting piece of this as a showrunner, writer, producer is the whole James Bond aspect where you could imagine a version of this show where he's auditioning to play a James Bond-esque character that would not hit as hard. We did that. No, we did that. That was, yeah, no. I mean, whether we were going to get the Bond and how much of the Bond piece we could use was an open question for a big part of this. And we just kind of will to power it. I give Riz a ton of credit. Before Amazon was the decision maker in this, we had to go and answer Barbara Broccoli, and he did that and he wrote her a letter and he met with her. We shared scripts with her. She gave very thoughtful feedback. So we got her blessing, but we had, we're pretty far down the road. We have written scripts and it was going to be a big problem if she said no. So yeah, but we talked about, okay, what is the version where it's Bond, but we never say Bond. And I was just like, that version isn't as good. I mean, it's like when you're drinking beer and it says beer on it on the TV, it just takes you out of it. It's just not the same. Exactly. So we really wanted to make sure, and again, we were respectful and we didn't want it to be a parody. We didn't really want it to be something that we never even remotely considered using the Bond music or using any of their kind of cinematography, the iconography, the circle, and the, all that stuff. We wanted to like hint at but never exactly use. We just thought it'd be a smarter, kind of cooler way to go and also would avoid obvious, more thorny IP issues. And then it was really interesting when Amazon kind of became the actual decider on the Bond. They took over from the Broccoli family for anyone who doesn't know the IP of James Bond. So now anything future James Bond stuff could exist through Amazon. Yeah. I mean, one of the ironies of the show is that people who obviously don't track this stuff the way you might or I might think that this is all part of Amazon's like master play and a rolling out bond. Well, that couldn't be further from the truth. I mean, maybe. Well, I mean, in a backdoor kind of way, I guess. Yeah. You know, certainly not in the inception. We had, you know, written the show. We had shot the show. We were all the decisions were made pretty much when that thing came down. And then it was just to put honestly, it was really just a question of like, how much of the marketing are we going to market off the back of the Bond stuff? And again, Amazon was incredible. And not just saying that because they're listening in Amazon was incredible. They just absolutely I mean, they had natural hesitation since anyone would hold this like priceless piece of IP, but they were so supportive and just kind of let us do it our way. And there was very little I mean, there's some things that we kind of deliberated, but there was very little that they put their foot down and said absolutely no to. And we kind of did the version that we wanted to do. Yeah, it is pretty funny that now this show, Bate, is the first James Bond TV show on Amazon that I was been wondering, what's that going to be? You know, how are they going to do a Bond show? And you guys did it already. Yeah. Yeah. I mean, yes. I mean, it's certainly not the Bond show that they would do if they were developing a Bond show. But it's a very nice complimentary piece. I mean, in a, you know, in a perfect world, it's like when, you know, Tom York goes off and makes a cool side project that's definitely not radio head, but it still fits in the canon of that work, you know, like that's the kind of the dream is to kind of be something that is like complimentary, but not really crossing over in that way. The other absolute coup that you pulled off is this voice cameo performance from Patrick Stewart that's gotten quite a bit of attention. Can you tell the sort of quick version of how that how that came together, how you got Patrick Stewart to play? I think we can say at this point, the show's been out long enough for sure. Voice of a severed pigs head. Yes. It's actually the Riz's character Shaw's critical inner voice, which when we were kind of when we were kind of talking about this in the room, this was one of those ideas, you know, like God bless the writer's room, you know, this is one of those ideas. I want to say with DIPICA, one of our writers kind of pitched it and we really liked it and we didn't know at the time how much we were going to be able to go with it and whether it was going to come back, you know, multiple times. And if we just found it really, really fun. And then of course, you're like, okay, well, he's this kind of striving, you know, you know, British Pakistani actor who's striving for like establishment, you know, credibility. What are the voices in like, you know, England that are like the definition of like that stentorian, you know, you know, grand doms level actor and you think of Patrick Stewart, you think of Ian McKellen, you think of these, you know, these kind of lions. So we made our list and just tried to get real about, okay, we're going to take a swing at one of these people who has the most recognizable, instantly recognizable booming voice that would also be funny when you throw in some of the insult humor that the character engages in. And it just was like, it's got to be Patrick Stewart. And, you know, with these things, it's always a little bit of a dance. But again, he was really responsive and complimentary. And it just worked out beautifully because he was coming to London for some Avengers stuff that he was doing. So it like, you're able to do all the sessions in person with him. It was like, one of the greatest thrills of my life by far, not just my career, I just sitting in a room with him for a couple of days, reporting this stuff. Was there a line that you got him to say that you can recall that really you couldn't believe you was coming out of his mouth? Well, there's one thing that he said that on the date on date, this is such a terrible thing for me to do it. I'm sorry, I'm gonna apologize right now, but I can't tell you what it was. But there's one thing that we got him to say that couldn't believe he said and then the next day he came back, he's like, you can't use that. Oh, no. So that's disappointing. Yes. But I think I don't want to talk to his wife or I don't know what, but like he basically came back was like, yeah, that's probably a bridge too far. Someone was like, what are you doing? Exactly. All right, so I want to go back a bit and talk about this earlier phase of your career. How did you end up becoming John Stewart's first head writer at The Daily Show? That's quite a feat. Yeah, well, it was, I had moved to Los Angeles as part of a writing group. I was the editor of the Onion newspaper back in the day. And I had moved, I'd left Wisconsin where the Onion was based back then and moved to Los Angeles with some of the other former Onion writers. And John Stewart was taking over for Craig Kilbourne because, you know, The Daily Show had a host before John. Right. Yeah. But it was a very different style show. It was not a show, to be honest. I was a huge fan of and we had done an Onion TV show that I really enjoyed as a pilot that Fox came very close to putting on the air, but they just never put it on the air. And that was being developed at the same time The Daily Show was being developed with Craig. So I kind of saw The Daily Show as this kind of like competition and lesser competition, to be honest. I was arrogant. But when I heard John was taking over, I was like, oh, that's really, really interesting. He wanted to change the tone of the show a little bit. And he really loved The Onion. And because I was kind of like the de facto, you know, leader of the group of guys in LA, my agent was like, do you want to meet with John Stewart about, you know, the head writer job at The Daily Show? And I was a little iffy on it. I mean, I love John. In fact, John was, we were developing other talk shows. We had a deal at Fox at the time. We were developing other, you know, late night shows. And all of our shows had John Stewart as like the model host. I was a huge fan of this. But I thought, in a weird way, that him taking over The Daily Show back then was like not like not even a lateral movement. It felt like a step down. I thought he was like a mother and a parent. And but I was like, I'll definitely take the meeting with John Stewart for sure. And I flew out to New York. I was living in Los Angeles at the time. And John and I just hit it off. We like bunch of some shitty bar on the other side and, you know, had a couple beers and just talked. And he told me what was, you know, kind of what he liked about The Daily Show, but what he wanted to do. And I was like, yeah, that's the version that we should be doing. We should be doing a show that's about the news, not about just what's funny in the news. So we kind of like just had an immediate meeting of the minds that like the show, you know, the way that the onion was kind of a bizarro world New York Times, like The Daily Show needed to be reflective of what was on television, what was in the newspapers, and what people cared about. And that was something we instantly connected on. So another morning, another reminder, there's a gap to be careful of. But maybe it's time to bridge the one between your nine to five and your dream of living life on your own terms. At HSBC, we know ambition looks different to everyone. Whether it's retiring early or leaving more for your family, we can help because when it comes to unlocking your money's potential, we know wealth. Search HSBC wealth today. HSBC UK opening up a world of opportunity. HSBC UK current account holders only. I had never worked on a television show on a staff on a television show before I got the head writer job. And, you know, I took the job, but I was like, I'm keeping my apartment LA, I don't know if this is going to work out. I don't think this show has necessarily has the legs. And I moved there, I made a ton of mistakes at the beginning. But John, to his, you know, ever loving credit kind of stuck with me, I was 27 years old, I was way too young to have that job. Most of every writer on the staff was older than me. And they've all rightly felt that they should have had the job, not me. It was very tough. The first year was not enjoyable. But we kind of started to see some like, improvement in the way people responding to the show. We were like, people were just having a different reaction to it. There was definitely some tension in those early days, because again, it wasn't totally a broken show. Like, why are you coming in here and changing all these things? But John and I really formed a really good team in those early years. And he just totally had my back during some kind of rock transitional times. And yeah, we had them the show took off after the election of 2011, just kind of became something that neither of us could have ever imagined. Yeah. And then within a few years after that, you're helping to launch the Colbert Report, which for me, was an even more sort of important influential show. It came out while I was in college and I was just obsessed with it from the beginning. How did you sort of think about that as a new challenge and something different? And what are your memories from that sort of first launch of doing that with Colbert? Well, I mean, in those early kind of years after the Daily Show had really kind of found its voice and found its legs, we were really feeling it. We really, really thought we could do, this book that we did really well. That was like this big New York kind of a thriller. Yeah. And we were feeling like, okay, we got this. And we had this incredible staple of correspondence. Steve Carell, Stephen Colbert, Rob Cordray, Ed Helms, Samantha B. It was just like a real, you know, murderers row of people were like, we need to, we're going to lose these people. And we had already seen people coming after Carell to, you know, he was in a Will Ferrell movie, he was in a movie with Jim Carrey, he started to get these like, you know, really juicy, not lead, but like second lead roles. And he's like, he's going to be a star. He's either going to be a star with us, or, you know, he's going to be a star on his own. So we had this section, this segment of the Daily Show that we did with Carell that was like super silly. It was like this green grocer, it was a real throwback section. It was almost like a local news piece, where someone comes in and talks about like the produce that's fresh each. I mean, it's a really, it was a really weird segment. And it was produce Pete, it was called. And we wanted to do a produce produce Pete spinoff show with Carell. And he was like, no, I think I'm going to go do the office. Yeah, sounds great. But yeah. But we lost Carell. And we're like, we have to lock down Colbert. And we had done, we had done this section as like a joke. We had done this like almost like a fake advertisement for this show, the Colbert Report, which is just like a straight like this take on O'Reilly, who was like a big cable news guy back in the day. And we were like this, we think this can be a show. And it was like, we get it enthusiasm because it was like this like really, really cool side project that used all the tools that we were kind of using on the daily show, but filtering it through like a different comedic voice and a different comedic muscle. I imagine it's like, when professional athletes like discover like, oh, I'm really good at baseball too. You know, like it's a whole other sport, you know, and it was so much fun developing that show. And I think Comedy Central was like, we don't know if this thing is going to work long term. I think it's really funny, but it does that character have, you know, kind of like staying power or people could just get sick of it. And Colbert is such a fundamentally decent human being. He's such a good band that he was like allowed to be like, you know, batshit crazy and say horrible things, but you kind of always knew where he really was on it. So like that the success of the show kind of existed in that tension between like the absurdity of the character and the reality of like his like radiating decency. And it was like a show like the pilot was like a perfect pilot. And yeah, truthiness. Yeah, exactly. And after the pilot, they had given us like a four week or, you know, three week trial run. And I think after like the second episode, they picked it up for the year. They're just like, we were wrong. This is great. You know, so yeah, that was really, really satisfying. Yeah, it's funny. You mentioned John Stewart as you thought he was the heir apparent to Letterman. And then of course, Colbert ultimately leaves Colbert rapport after I think nine years, which was incredible that he was able to sustain the show for that long, I think. And he said he's talked about how hard it was. And then he goes to the late show. And I'm curious what you made of his move from Colbert rapport, which you were not involved in anymore at that point to the late show, because it was a very different guy that we were seeing, you know, I think he's obviously still gone very hard on politics, but in a very different way, you know, in a very sort of more mainstream, you know, late night monologue way versus this character and this sort of really hard satire of the Colbert rapport. So what was it like for you to watch him make that transition? Well, I mean, doing these shows, I mean, Colbert writing Colbert, you know, was the hardest late night show that you could possibly write. I mean, there's no late night show that's going to be harder to write than that, because the whole show is being done character, basically. So everything, usually when you look at a talk show, you have these segments, sections, segments that are not filler, but it's like, when you're doing an interview, you can like, relax and just have a conversation. I mean, yes, there's some research that goes into it, maybe you have to watch the movie or read the book. But you can have, you know, 20 minutes of your hour long show be unscripted and casual. But Colbert was scripted, basically like almost wall to wall, really, really hard to do that on a nightly basis, like really, really hard. So the burnout factor is real. I mean, I got burned out. I mean, I was doing two shows, but I got burned out really, really hard. And the people, people stayed a long time. And it's just a testament to how dedicated and talented those people are, because it's really, really hard to maintain quality night and night out. But I think he was probably, you know, definitely ready for a new challenge, I would say. It was funny about John, because, you know, John was the heir apparent to Letterman, but I think because the Daily Show kind of became its own thing, it didn't surpass and nothing's going to surpass Letterman, because Letterman kind of broke the mold on what that was in that space. But, you know, I think John created his own lane. And at the time that he might have taken a shift over to that, it would have been weird, because he already was kind of, I don't want to say iconic, but iconic in, you know, in his own way. So it would have been a weird shift. I think the post Colbert was still doing his first thing. And it was a thing that was very mannered in particular. There was probably a larger appetite to be like, Oh, what's this guy going to be like? And you take off that character and let him be just him. So it made a lot of sense to me to make that move. I have a soft spot for, you know, for the Colbert Report, not just because I was there at the beginning, but just because it felt like it was really, really trying to do something different in that late night space. And when you go to these big institutional shows, you know, yes, there is some room to kind of with some of the details a little bit, but ultimately you're kind of a slave to that format. And you can make it your own. And I think Stephen has done a great job doing that. But I just am so much more partial to, you know, weird contests and just bringing in the audience and the whole idea of Colbert Nation. Like there was just so much about it that felt kind of ahead of its time. Yeah, exactly. Yeah, well, I have to say, I get excited a few times when he's sat down behind the desk and brought back the word on the late show, which is really, I think, you know, you're taken right back to that time. Yeah. You know, we're talking during his final run of episodes before he's taken off the air. I'm curious what your reaction to that was. You know, there's a lot of debate at the time about what the driving force behind CBS's decision to take him off was, whether it was directly political or not. And he's been, I think, a little bit diplomatic about it. But I'm curious what you think. Well, I would say that late night is kind of a dinosaur, you know, in the world of broadcasting, in the world of media. So I think all of these shows are probably kind of in their twilight one way or the other. I think that 100% it was political. There's just no, there's no doubt about that. But if the show was super profitable and there was a path forward, you know, to profitability, I don't think the politics would have mattered as much. But certainly, you know, if the show is losing money and all those shows basically lose money, then, you know, you don't really have a, you know, a leg to stand on in that situation. In a weird way, and Stephen and I had talked about this a little bit. It's kind of like a perfect situation in that, you know, he gets to kind of go out, you know, kind of do that retirement tour, do that, everybody knows he's going off the air. He gets to go off justifiably, not as a martyr, but certainly as someone who kind of, you know, kind of stood his ground and stayed true to who he was. And I think that he's going to have a galaxy of opportunities waiting for him to do something really interesting next than something surprising. And, you know, sometimes those jobs, especially if you're a comic, he's not a traditional comic. But I mean, if you're a comic, when you land one of these late night jobs, it's like, you know, you're made, you're a made man, you're set for life. And sometimes that can become a little bit of a prison. I certainly know something that John and I talked about all the times, it was amazing to have this buy for him. But it's also, you know, exhausting and relentless. And like the reward for doing an amazing show is you get to get up and do the exact same thing tomorrow and like be disappointed if it's not as good as the show you just did. And, you know, it's, it's hard. So I think the fact that there's like a, that there is this built-in kind of sunset for him, to me, it's kind of a dream come true. But I don't know if he, I don't know if he would just say it that way, but I feel like it's kind of a great situation because he's going to do something great next. Yeah, I feel like there was some speculation or hope on the part of somebody who was going to kind of go scorched earth on the way out. I don't think that's his, his style. What do you think? He's a classy guy. He's a classy guy. I mean, he, you know, I think he's capable of killing with kindness. I think what he doesn't say is sometimes better than what can be said. And, but I mean, he is just a class act. So I just don't think, you know, the end of the day, he, they paid him a ton of money. He got to do a version of the show that he wanted to do for a long time. He got to bring a lot of the people from the old show with him and everyone's done really, really well. They've got beautiful theater. It's been a, I mean, I think it's been a privilege. I think he would say that too. Yeah, obviously, it's a little icky the way things are shifting right now. It doesn't feel good just in terms of like comedy and, you know, just the political environment of where these worlds used to feel somewhat a little more separated. It's not a good feeling for sure. Yeah. Well, we know he's writing a Lord of the Rings movie, which is exciting. Do you think he'll do another political comedy show of some kind in the future? I mean, this is just pure speculation. Not soon, I don't think. I think that, I mean, I really love what Conan has done. I think Conan has just absolutely been brilliant and how he has, you know, taken the best part of what he does and found other forms for it. His stuff is interesting. It's dynamic. It's fun. You know, it's across, you know, he does a podcast and you know, he does these specials. And it's just like, you know, I love what Conan, I mean, I loved Conan's show. I love Conan. I just love what he's done in this period of his career. So I think that's a great model for any of these guys. So you said that you were experiencing some intense burnout when you decided to leave in 2006, leave late night, the Daily Show and the Colbert Report. I'm curious if you feel relieved that you left before Trump came on the scene or if you feel like you missed anything there because that's really changed late night in so many ways. I mean, I think about this all the time. But I am so happy I got out what I did because it feels like when I look back at what we were doing in 2000 and 2004, you know, really before, you know, Obama, I got out before Obama was elected. You know, there was just an innocence to it. There was a naivete, there was like a purity of a sort. And, you know, it wasn't cynical for us at all. You know, we were, you know, we were kind of earnest in a, you know, in a forgivable way. And then it all just kind of changed. And I think it would have been very difficult for me to kind of handle that transition. I don't think I would have done well. And there's been not a single moment where I wished I was back in that world since Trump came on the scene because I find it, you know, I personally find it so revolting that it's just hard for me to be like, I'm going to make a joke. It's not like there weren't things on all sides of the political spectrum that kind of annoyed me or bothered me or sickened me, you know, but there's just been a concentration, you know, in the last eight to 10 years that is just so unpalatable to me that I don't think I'd be able to just kind of like, hey, everybody, we're putting on a show. Like I just not sure I'd be able to do that. Isn't life grande and making it better just got easier with Starbucks new protein cold foam? A little something, something to take your favorite drinks up a notch with 15 grams of extra protein. Turn your usual iced caramel latte into a smooth iced caramel protein latte. Add a delicious swale on top of your drink, just like that. Protein never tasted so good with Starbucks new protein cold foam. Subject to availability while stocks last. Yeah, I mean, in that sense, were you surprised that John Stewart decided to come back in 2024 after he kind of missed the entire first Trump run as well? Not really. I think that the thing that was that I remember, and again, this was going back almost 20 years. So I mean, I remember is that, you know, being able to do the show but not with that pressure of every day, that was the real problem. Because there were just some days where you just didn't have it. You had a big writing staff and you had pieces that you could run and sometimes you could repeat a piece if you had to or do two segments with a guest, if there are interesting guests, there were things you could do to kind of you just didn't have your A game. But you're doing a show every day, it's just really hard. So when he came back one night a week, I was like, yeah, that's what he wants to be doing. You could put all your energy into one killer show. And we had talked when we were in our kind of like, are we going to do this forever kind of mode when things were really kind of blowing up and seemed like there were lots of opportunities, we had talked about basically doing what John Oliver did. You know, that was another guy that we had, John Oliver, Jesus. Yeah. So we, you know, the John show on HBO, John Oliver show on HBO was a show that John and I talked about, like that's a show we really want to do when we just can't do the daily show anymore. But you don't always get to dictate that. I mean, the show's a big success on Comedy Central, there's no way they're going to be like, yeah, you can do it one night a week when we get you forward away. So like, it wasn't really an option. But I think we looked at John's show, Oliver show when he started, it's like, that's like the evolution, like he's like more thoughtful, more researched, you know, you can write for a whole week and you just like, you know, blow it out, you know, once a week, it's a really nice model. Yeah, it's kind of what John's doing now is this sort of, he's doing like nearly 20 minutes plus once a week on a one or two topics. Yeah, exactly. So before we go, I want to run through some of our sort of speed round questions with you. Starting with, is there something looking back at your career that you wish you could say yes to that you said no to at the time? Wish I could say yet. Oh, man, well, I had a moment where the logistics were very tricky. And I really wanted to work for the show 30 Rock. I love 30 Rock. I thought it was probably the best comedy of, you know, my era, you know, just in terms of just a really, really, really funny, fast, interesting show. And the problem was when it was on the air, I had moved to Los Angeles and was married and had family and just couldn't do that to them. And it wasn't like they were like beating down my door, but there was a moment where I was, I could have maybe gone and worked on 30 Rock. And I would have really liked to have worked on I love working on Modern Family. It was a great experience. 30 Rock was probably more my speed, you know, comedically. But one was in Los Angeles and the other was in New York. And, you know, I needed to be a Los Angeles during that period. On the flip side, is there anything you said yes to that you wish you could go back and say no to? Anything I said yes to that I would go back and say no to. I mean, I think every writer, not every writer, but 99.9% of the working writers out there have probably taken some jobs for money that are not jobs that they necessarily would want to put at the top of their IMDB page. I mainly have steered clear of a lot of those jobs, but I have done some rewrite work for some, not particularly good animated movies. This was earlier in my career. But I didn't always feel great about that because I wasn't a big fan of some of the movies. They were either sequels or just kind of, you know, things that needed, you know, needed a lot of help. And I just felt like I'm not a good hired guy in that way. Like it just doesn't feel great to do that. I'm not passionate about these characters or this world. And these, you know, these people who are hiring me deserve someone who like loves this shit, you know, and I wasn't that person. And those were times where I kind of had those like long, lonely drive, you know, drive home from the studio or like, what am I doing? You know, like, I thought I was trying to do something that spoke truth to power. And now I'm writing a duck that's a little vulgar. At the height of the Daily Show time there, you got to write on the Oscars when John Stewart hosted. Is there a story or memory that stands out from from that experience? I mean, a couple, the best one was we had written these attack ads, the political style attack ads. And they were pretty harsh in their tone because they were trying to mimic the kind of tone of, you know, the hard, you know, political attack ads of the day. And we had to, we wrote one for the best actress category. And it was directed at Charlize Daron, who was nominated for, oh man, I can't remember the movie where she plays the monster. Yes. And it was, I'm going to screw up whether it was Kieran Knight. I don't know who was attacking her. Basically, the thrust of the ad was that Charlize Daron was afraid to act while hot, you know, like that she had to make herself ugly in order to be a dramatic performer. And it was, it was like, that's not a true statement because Charlize Daron was an amazing actress. But like the ad was a little harsh and we had to bring it to Charlize for her approval. And we, I just remember standing there with, you know, me and the other writer with her reading it. And you can see that she had to be a good sport about it. But she wasn't really, she didn't like just busted her ass, given a thread over four minutes of these, you know, these jerks are basically like telling her that, no, you're hot, but you made yourself ugly. You know, it was like, and just standing there, it just felt like it was like a page and a half, two pages tops felt like forever. She read it and to her credit was like, yeah, this is great. This is funny. And she let us off the hook. But that was one of the more, yeah, you definitely like having that distance is always nice. They say never meet your heroes. And I'm wondering if you have a story that either proves this right or wrong. Hmm. Well, he recently passed away. But there was a time when Val Kilmer was really, really, I love, love Val Kilmer. I love top secret. I love him in Tombstone. I mean, love him in the doors. I love Val Kilmer. And even real genius, even like really cheesy stuff related to Square, I love Val Kilmer. But he got to be a little eccentric and odd at a certain point. He got just like obsessed with Mark Twain and was kind of like a little bit on the outs in Hollywood. And he started hanging around the TV show offices. And like, and like, we just got to show up and like hang out sometimes and like, Val's here. And like, I really enjoyed talking to him, but I could definitely feel like, you know, he was just an odd guy in like a career transition of the moment. And I was like, you know, we had to get back to work. And I was like, I think we have to kick Val Kilmer out of our offices so we could get back to work or who's going to do that. But so that was probably the closest to meeting your hero and, and then having to walk it back a little bit. Yeah. When you look back, is there a story from your career that makes you laugh now, but was really not funny when it happened? Makes me laugh now. Wait, is it asked that again? So a story that makes you laugh now, but really was not funny when it happened. So it's sort of like, you know, tragedy plus time equals comedy. Wow. Well, when we first, so when the Daily Show first started getting a lot of attention, it was not in the writer's guild because late night on basic cable, this is how, you know, old this is late night on basic cable was outside of the writer's guilds. They were like a guild sanctioned thing. So everybody who had to wrote for those shows couldn't be in the writer's guild. When I was hired, I was in the writer's guild. So that was a problem. And the solution was for me not to take a writing credit on the show at the beginning. So I when I was the head writer of the show, I didn't have the title of head writer. I had like senior producer, some like stupid made up title to avoid running a foul of the guild's rules. And then the show by nominee for best writing for the first time. That was like the first time like a basic cable show ever got that. And we won. And I didn't get an Emmy. I was like, God damn brutal. Yeah. I was like, Oh, I probably should have figured out a way to address this because this is a lot of work. It's tough. You weren't thinking about that. Yeah. I wasn't thinking about that when I took the job. I was just like, All right. Thank you again to Ben Carlin for that incredible conversation. As I said, I've been a fan of his work for so long. And I really hope you enjoyed hearing all of those old stories about the Daily Show and the Colbert Report. And definitely check out Bait on Amazon Prime Video as well. It's six episodes. They're short. They're so funny. They're so different and interesting. And Riz Ahmed is fantastic on that show as well. If you're enjoying this podcast, please follow us on YouTube at the Obsessed channel. We want to hear from you. Leave us comments. Give us your feedback. You can also leave ratings and reviews on Apple podcasts and Spotify or wherever you list the podcast. And please follow us there as well. Thank you to our producers, Rachel Passer and Devin Rajarino. We will be back with an all new episode of Obsessed the podcast very soon.